


Falling with Style

by ohboyohboyohboy



Category: Supernatural
Genre: Alternate Universe, Bets & Wagers, Bickering, Castiel Acts Like Endverse Castiel, Castiel is a Tease, Dean Flirts, Drinking & Talking, Firefighter Dean, Flirting, Fluff, Fluff and Humor, Human Castiel, Humor, M/M, Romantic Comedy, Scared Dean, Skydiving, Snarky Castiel, Teasing, Texting
Language: English
Status: Completed
Published: 2017-06-07
Updated: 2017-06-07
Packaged: 2018-11-10 03:53:25
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 9,399
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11119359
Author URL: https://archiveofourown.org/users/ohboyohboyohboy/pseuds/ohboyohboyohboy
Summary: Cas looked back up at Dean.“You sure you’ve never done this before?” he asked.“Yes. I’m sure I have never been skydiving," Dean muttered miserably.“It seems like you’ve got some experience getting harnessed up.”Dean squawked. Cas bit his lip to hold back his laughter._____After Dean loses a bet with Sam, he has to go through his worst nightmare: boarding a rickety plane and tandem skydiving out of the stupid thing. It's a shame his incredibly sexy, snarky professional skydiving partner is such a tease about it.





	Falling with Style

**Author's Note:**

> So.  
> This happened to me.  
> Very recently.  
> A lot of/some details are not true - I didn't get with this dude and all, but oh man. Skydiving is INTIMATE, Y'ALL.  
> I'll leave which parts are true and false up to you ;)
> 
> Also, you should all skydive if you can. I am petrified of heights, and it was one of the most incredible experiences. NO PRESSURE THOUGH.

Dean was starting to shake. Like really, physically starting to shake, and he knew it wasn’t the normal, “I just sucked down three cups of coffee because the fire department had 4 false alarms last night” kind of shaking or the, “Sam just told this hot guy the story about the stain on my high school prom jacket and I’m very much struggling not to punch him” shaking.  
  
Dean was about to jump out of an airplane.  
  
So it was that kind of shaking.  
  
He thought back to what Jess had told him outside the fire station before driving him to this god-forsaken rinky-dink airport.  
  
“Breathe deep,” she had said, brushing a hand up and down his arm. “You know you’re way more likely to get hurt doing what you do for a living than skydiving, Dean. Everything’s going to be fine.”  
  
“Statistics are all bullshit.” Dean felt every word coming out of his mouth like vomit, fast and bitter and with his throat closing up. “I know how to deal with a house fire, this is completely fucking different –“  
  
“Stop thinking about it then!” she berated him, fondness in her eyes. Closing her eyes and raising her hands to her chest, she mimicked taking an excessively deep breath and motioned for Dean to join. He struggled to contain his eye roll and complied.  
  
How Sam ever convinced her to marry him was really beyond Dean.  
  
It was all Sam’s fault anyway.  
  
Fucker.  
  
Just two months ago, Sam had won his argument with Dean to join him at the fire station. Dean had been pushing for him and Jess to – well certainly not to move out of Lawrence, but not just to end up on the same path he was on, the same path his father had been on and Bobby had narrowly left for retirement a year ago. Sam had sat calmly at his kitchen table, Dean pacing back and forth like a Labrador looking for bacon scraps.  
  
“Sam, this is – no. I just – no. Why do you want to – to leave law? You’re acting insane, you’re planning on having kids, this is the stupidest –“  
  
Sam had let Dean ramble on, wearing a hole through his kitchen floor for 45 minutes before stopping him. “Dean. I want to do this. I’m not helping people at the firm right now – I haven’t been for a long time.”  
  
Dean felt himself starting to lose the argument.  
  
Sam sighed and looked up at Dean with that look that could only scream ‘pitiful justice puppy.’  
  
“I want to help people. To save people. And after mom… this isn’t about that – for either of us – but I know you know how this feels.”  
  
And there it was. Argument lost. Goddamnit.  
  
And then of course, rapidly came the had-to-be-expected brotherly friendly (but-not-at-all-friendly) goading and bickering in the firehouse.  
  
**Six weeks ago**  
  
Dean couldn’t believe what he was hearing. His brother, his own blood, was sitting across from him at the Roadhouse – the _Roadhouse_ for god’s sake! His bar! – telling him his training records were shit. Was he so drunk that he was mishearing shit? Was Sam drunk enough to be saying this in the first place?  
  
“You know what Dean? I’ll bet your ass I can beat every single record you set during training. Every. One.”  
  
“Really?” Dean had said. “Really?! Because now, you think you can beat my run times –“  
  
“Oh I know I can beat your run times,” Sam sloshed his IPA, earning him a quick ear-tug from Ellen across the bar.  
  
“Boys, settle your asses down.”  
  
They’d pretty much raced each other to Ellen’s bar right at 8pm when their shift ended. Bobby and Rufus had joined, a little further back, cackling at the brothers shoving past each other in their ridiculous sprints for pride.  
  
Dean had to admit – he had hated the idea of Sam putting his life on the line every day for work. But this much time together, quality time with his brother, kind of made him feel like a kid again. Running and yelling and teasing and having fun - doing the kind of shit brothers did growing up when they weren’t dealing with a widowed father and some serious heroism issues.  
  
Not that he would ever tell Sam that. _Eugh._  
  
They spent at least 30 hours a week together now – more or less depending on when their shifts lined up. Did every single call Sam went on scare the living shit out of Dean? Obviously. Did he start spending half of his emotional energy on making sure Sam stayed out of the truly life-threatening shit? Um, duh. And did every possible chance for competition spur the two of them into little-league style squabbling? More than he had thought actually possible.  
  
But it was fun. You know, in an annoying kind of way.  
  
“Are you hearing this, Ellen?” Dean said. Yelled maybe. Was he being loud? I mean really, who’s to say. He turned back to Sam. “Why don’t you put your money where your mouth is, rookie? You know your record with losing bets to me –“ he whipped around to Ellen, “He _knows_ – he _knows_ his record with losing bets to me.”  
  
“Uh huh, I’m sure.”  
  
“Dean, if I don’t beat your truck-load record tomorrow, I – I’ll buy you a beer.” Sam was laughing at him.  
  
Dean laughed right back. “You beat my truck-load record tomorrow? Yeah right. I’ll take that.”  
  
“Fine.”  
  
“Fine!” Dean took Sam’s hand and shook it.  
  
Dean lost. Which of course led back to the Roadhouse the next Tuesday when they both had off work.  
  
“I hope she watered it down,” Dean said, handing Sam the stupid craft IPA he wanted.  
  
Stupid beer. Stupid Sam. Stupid fucking truck.  
  
“Excuse me? Are you accusing me of somethin’ there, Dean?” Ellen said, cocking her head and glaring playfully at Dean, who wrinkled his nose and mumbled an apology.  
  
“Well, thanks Dean,” Sam said. “I’m glad you’re taking this so maturely.”  
  
“I’ll just have you know though –“  
  
“And here comes the justification,” Sam said, turning back to Jess, who was seated on his other side and sipping from some ridiculous fruit beer. He liked Jess and all – he really loved Jess – but ordering a shandy? A lemon shandy? Come on.  
  
Dean grunted and fidgeted with his drink napkin. “I’ll have you know that my boots were like – like two sizes too big for me when I set my record. You beating it is just because of your giant yeti feet fitting in the stupid training boots.”  
  
“Fuck off, Dean,” Sam laughed, grinning and sipping from his cup.  
  
Oh man, Dean really wished Ellen had watered that down.  
  
“It’s not like that training record means anything either, you know. The big ones – the run tests and the, the lifting and climbing shit –“  
  
“The other ones I’m going to beat you at?”  
  
“Yes – NO. Those tests, but yeah – those are the important ones. The big ones.”  
  
Sam grinned, “Yeah, Dean? And what would you say if I beat you at every one of those?”  
  
Ha! Laughable. Laughable! Ridiculous. Just ridiculous!  
  
“You beat every one of my records, Samantha? I’ll jump out of a fucking airplane.”  
  
  
Two weeks and four new records later, Sam grinned at Dean, dripping with sweat and taking off his helmet in the entry way of the firehouse.  
  
“Ready to jump, jerk?” he had said, laughing and swaying as the rest of the guys clapped him on the back. Traitors.  
  
“Look, Sammy – you did great. I’ll give you that and all –“  
  
“ _No._ Uh uh. No backing out of this, Dean – you took this bet, you made the deal.”  
  
Dean stuttered, torn between A. a rant of frustration and anger about the overblown, ridiculous bet terms and B. literally begging for any possible way out.  
  
“What –“ Sam said, his mouth dropping into a goading smile. “You can’t do it?”  
  
Dean pursed his lips tightly.  
  
Shit.  
  
SHIT.  
  
  
**Present day**  
  
It had taken four weeks of postponing – schedule conflicts, weather conflicts, personal and professional conflicts (including 5 different “haircut appointments” that Dean just absolutely couldn’t move, which Sam let slide given how obviously Dean stumbled over the reasoning with each additional lie.) Eventually though, it had to happen. Sam set up the final flight date and time – even dialing the phone number put an ice in Dean’s chest.  
  
“12:30 on Wednesday, April 23rd,” Sam said, gripping Dean on the shoulder.  
  
“Peachy,” Dean spat in response.  
  
  
It was 12:29 on Wednesday, April 23rd, and Dean was still sitting outside the airport. Breathing deep.  
  
Totally not hyperventilating.  
  
What had made it worse was Sam’s stupid speech two hours before.  
  
“Dean, I –“ he stopped and pursed his lips and looked back up at Dean slowly. Meaningfully. _Ugh._  
  
“Dean, if you don’t want to do this – if you really don’t want to – I get it. I know you’re scared. And I’m –“  
  
_'Oh please don’t say it'_ , Dean thought.  
  
“I’m here for you, Dean. And I’ll love you whether you jump out of that airplane or not.”  
  
“Ugh, UGH, COME ON” Dean roared. “Oh my GOD, let’s just fucking get this the fuck over with,” Dean had stormed past him, his groan ripping out of him. He thought he might have heard Sam cackling behind him, but he wasn’t sure. The ringing in his ears had gotten too loud.  
  
He looked out through the windshield at the little metal sign.  
  
_“Lawrence Skydive – the #1 dive in Kansas!”_ it read. Dean felt his entire face scrunch up. Sam and Jess pulled into the parking space next to him and Dean managed to pull himself together if only for his pride, and he felt a flare of pissy anguish as he saw Bobby, Jo, and Rufus step out of Sam’s Prius from the backseat.  
  
“Who else did you invite, Sam, the entire fucking Lawrence population?”  
  
Sam grinned. “We’re here to support you, dude, we’re not here to throw you out of the plane ourselves. Now come on, you’re going to be late.”  
  
When Dean opened the door to Lawrence Skydive, he was quite severely underimpressed.  
  
“What the fuck is this, a trailer outside the airport?” he thought to himself. The thin metal walls that had appeared to be attached to the tiny airport building seemed less to be a part of the solid structure and more like a mobile home that had been tacked on as an afterthought. “Encouraging,” he mumbled.  
  
“Quit overthinkin’ it,” Bobby said from behind. “You made your bed, idjit.”  
  
Dean wished that every one of them had their beers watered down for the rest of their fucking lives.  
  
A young, dark-haired woman sat at a desk bizarrely close to the door, working off a clearly-personal Mac laptop and sighed as Dean walked in. Actually sighed. _What the fuck?_  
  
“Hi. I’m Meg. Welcome to Lawrence Skydive,” she spoke, a false cheeriness in her voice that Dean would’ve probably tried to flirt around had it not been for his determined focus on keeping his voice from shaking.  
  
“I um – yeah. Hi. I’m Dean.”  
  
“Oh yeah – yep. You’re the last one of the day.”  
  
Dean started at that. “But – it’s noon. Is that – that’s normal?”  
  
She rolled her eyes and stared back down at her computer. “You’re purchasing video footage with this, yes? Someone named…Sam gave me his billing information for that.”  
  
“Oh, yep! Yes, definitely video. Definitely,” Sam said from over Dean’s shoulder. Dean struggled not to reach around and break Sam’s nose.  
  
She glanced up from the laptop. “You and your – group – can sit over on the couch,” she said, glancing at the whole posse. “Cas will be here in a second.”  
  
“Who… is Cas?” Dean mumbled, regaining some mild composure after a possibly not-subtle voice crack.  
  
“That would be me!”  
  
Dean turned around to follow a cut-glass gravel voice coming from the sliding metal door at the back of the trailer. For a split-second, Dean wasn’t thinking about the skydive – this man was fucking gorgeous. Bright blue eyes, BJ lips that rivaled anyone he’d ever seen outside of his own laptop, and a thin, toned frame under a sly grin.  
  
“I’m going to be your tandem skydive professional today,” he said, walking over to Dean with a kind of unexpected cockiness and jutting his hand forward. Dean shook it and tried his best to seem confident.  
  
Or at least not to let his voice crack again.  
  
“Have you ever done this before – um…”  
  
“Dean,” Dean clarified, clearing his throat. “Dean Winchester.”  
  
“Dean Winchester,” the man repeated. “You can follow me to the back. Are your friends coming too?” he asked, raising an eyebrow. Dean emphatically said no.  
  
“Meg, will you give the –“ he paused, “audience here directions to the landing site?”  
  
“Sure thing, boss man,” she said, leaning back in her chair and pulling out her phone.  
  
Cas proceeded to drape his arm over Dean’s shoulder and walk him towards the back door.  
  
_'Maybe this won’t be so bad. I mean…I’ll be strapped to this guy. Really strapped,'_ Dean thought, allowing himself a small moment of comfort.  
  
_'Strapped to a guy…falling out of a plane.'_  
  
Moment ended. Comfort gone. Dean felt his throat start to close itself up again.  
  
“You ever done this before, Dean?” Cas asked, opening the door for him and letting him walk into a smaller back room with a TV set and a coffee table with some forms.  
  
“No – no, um,” Dean started. “To be honest, man, I’m really only doing this ‘cause I lost a bet. I’m not super stoked about it.”  
  
Cas sat on the far end of the couch (futon really) away from the TV and swung his feet heavily up onto the coffee table. “Oh yeah?” he said, motioning for Dean to sit next to him.  
  
“Yeah,” Dean replied. “I’m not a huge fan of flying. Like, at all.”  
  
Cas’ grin widened. “Well, don’t worry. This stuff works almost every time.”  
  
“I know, I – wait, what?” Dean felt his heart fall into his stomach.  
  
_Almost…every time?_  
  
“Yeah, I mean – I won’t lie to you and just say, ‘Oh, it’s perfect, there’s no chance you’ll plummet and die’ but it works. Almost always.” Cas threw his hands up over himself to stretch upwards.  
  
“I – excuse me? I mean, is – how often –“  
  
“Look man, we all have to go sometime, right?”  
  
“Not today! Not – not from this!”  
  
Cas flicked an eyebrow. “How did you expect to die?”  
  
“I – from – what?” Dean could feel his eyes bugging out of his head.  
  
“I mean, obviously I know the statistics. You’re probably going to be totally fine. We, I mean,” he added with a slight tilt of his head down, looking up through his eyelashes.  
  
Dean huffed. “I just –“  
  
“All I’m saying,” Cas interrupted, “is that it’s stupid to think nothing will kill you. I mean you’re jumping out of a plane, right? Even if the parachute opens, there are like a hundred things that could go wrong, Dean.”  
  
Dean had no words. No fucking words.  
  
“Are you trying to get me to back out?”  
  
“Oh, of course not! No, Dean,” Cas swung up off of the couch and clapped Dean on the back, waltzing himself over to the TV and popping in a quick VHS before hitting the play button.  
  
Cas grinned at him. “We’re going to have fun, Dean. Now just watch your training video – I have to print your waiver forms.”  
  
Dean watched Cas leave the little office and slammed himself back onto the couch, letting out a huff of distraught breath. What was this guy’s deal? Was he deranged? Was he some sort of airplane-based-cult leader trying to torment heroic firefighting citizens into killing themselves?  
  
Okay, maybe that’s a little much.  
  
Dean then proceeded to watch the most 1980s video he’d ever thought possible where an old hippie with a foot long beard talked about why he wouldn’t be allowed to sue if he died.  
  
Fucking right. Sure.  
  
Cas – his professional fucking tandem skydive partner and possible sadist – strolled back into the room with a small stack of papers and pen, tossing them into Dean’s lap. Dean looked up at him – he had stopped caring that his mouth was hanging open and his eyes were bulging during the part of the video where the hippie said the words “possibly dismemebered.”  
  
“So just fill those out. Then I’ll get you all saddled up.”  
  
Dean inhaled. “That was the training video?”  
  
“Mmmm,” Cas sang. “Not training so much as just preparatory. You know how it goes.”  
  
“I really don’t,” Dean deadpanned in response.  
  
“You know, I’ve heard that the sooner you fill out your paperwork, the sooner we get to jump, Dean.”  
  
“Oh, what a joyous thing to look forward to,” Dean growled. Fuck this guy.  
  
“It really is,” Cas grinned, struggling not to laugh at Dean.  
  
God, if their parachute didn’t open, Dean was going to spend his last living moments fucking strangling this dude with the cords.  
  
Dean looked through the paperwork.  
  
_“Initial here, stating that you will not sue in the event of…”_  
  
_“Initial below indicating your understanding of the dangers of…”_  
  
_“Sign below indicating your emergency contact information is up-to-date and accurate…”_  
  
Dean’s signatures and initials got increasingly more wobbly as he worked his way through the 12 pages of bullshit.  
  
“Is all of this – is this really necessary?” he looked over at Cas, who had once again thrown himself back on the shitty futon next to Dean.  
  
“Oh yeah, of course. I mean, you know – in case of death.”  
  
“Dude, you are being incredibly not-chill right now,” Dean spat.  
  
“You’re going to be fine, Dean,” he said calmly, giving him a moment to keep eye contact.  
  
Goddamn, this guy was a truly beautiful piece of shit.  
  
“Probably fine, at least.”  
  
Dean threw the pen onto the table.  
  
“Done with your paperwork, then, great!” Cas said, snatching the papers out of Dean’s lap and carelessly tossing them into a filing cabinet.  
  
“Sweet organizational system. Seems like you’re real professionals here,” Dean scowled, feeling his nostrils flare.  
  
“Seems like you’re a little nervous, Dean.”  
  
Dean felt himself splutter and threw his hands into his hair. “Nervous? Really? You don’t think that’s because some fucking – some guy has been poking death threats at me since I got here –“  
  
“Well that seems like an exaggeration.”  
  
“- And, and I’m about to jump out of a fucking plane! I don’t even like flying to other cities! In the country! In big planes with seatbelts, that I can actually land in on the ground while still being in the fucking plane!”  
  
“I mean, those can kill you just as easily so that comparison seems a little illogical.”  
  
Dean whipped around to Cas and poked his finger into his chest, “Look man. I’m fucking terrified right now, and you are so. Not. Helping. Things. Okay??”  
  
Dean expected the small sigh that came out of Cas, the semi-patient huff that came often after a Dean-Winchester-Outburst. What he didn’t expect was for Cas to quickly grab him by the wrist, Dean’s finger still poking into Cas’ chest, and give him a look up and down.  
  
A look up and down that Dean normally expected after two drinks and dancing.  
  
Dean felt his mouth fall open and blinked rapidly. Cas tilted his head at him and the corners of his mouth turned up, almost fondly. They stood there in that second, Dean waiting desperately for words of comfort – any fucking words at all really – before Cas looked back down at Dean’s feet and took a quick breath in and out.  
  
“Your video is going to be real fun, isn’t it?” he asked quietly, almost mischievously, a toothy grin spreading over his stupid fucking beautiful face. “Alrighty! Let’s get this process moving.”  
  
Dean felt his face contort in confusion. Cas grabbed him by the hips and spun him around to face the door, hearing him reach back and grab some kind of clanging metal and fabric.  
  
“Time to get you set up in your harness – you’ve got your closed-toed shoes on, so no need to worry about that. Step in.” Cas reached his arms around Dean, holding a long black harness with straps for the feet. With only a slight moment of confused pause, Dean slid his feet into the holes.  
  
“Great,” Cas said quickly, walking around Dean and sitting back on the futon. He grasped Dean by the hips again and yanked him forward. Obviously Dean noticed where the man’s face was in relation to – I mean, to him. To himself. Ugh, he was confused.  
  
Cas bent forward ( _‘What the hell is going on’_ Dean thought to himself) and grabbed each of the straps around his feet, tugging them upward around Dean’s thighs and tightening the buckles and straps until the harness stayed put by itself. The tightened black bands pulled and pushed him forward and backward, Cas clearly focused on his task to the point that Dean felt a little manhandled.  
  
Cas stood back up and shoved Dean to face the other wall.  
  
Okay, so maybe more than a little manhandled.  
  
Cas ran his hands over the shoulder and chest straps draped over Dean, tightening and pulling and yanking all the way up and down. Dean could practically feel the man grinning from behind him, and the stupid sly grin was confirmed when he whipped Dean around to face him again. After jiggling the harness to test for movement a last few times, Cas looked back up at Dean.  
  
“You sure you’ve never done this before?” he asked.  
  
“Yes. I’m sure I have never been skydiving.”  
  
“It seems like you’ve got some experience getting harnessed up.”  
  
Dean squawked. Cas bit his lip to hold back his laughter.  
  
“Alright, Dean Winchester, let’s do the basic training.”  
  
Training. Yes. Training was formal. Training was something Dean could do.  
  
“When we start to get out of the plane, you’re going to hold tight to your chest straps right here –“ Cas gestured vaguely over Dean’s harness.  
  
Dean quickly grasped the straps. “Right here? Or above – or, or below?” he asked.  
  
Cas waved him off with his hand. “Eh, you know, anywhere. It doesn’t really matter.”  
  
If Dean’s eyes bulged anymore that day, he was concerned they were going to pop out of his skull.  
  
“You’ll grab those straps, and I’m going to need you to shape yourself like a banana.”  
  
Dean blinked. “A…banana.”  
  
“Yup.” Cas turned to the side and motioned for him – tightening his body and leaning in a slight backbend. “Banana.”  
  
“Banana.”  
  
“Yes.”  
  
“…Banana.”  
  
Cas tilted his head again. “...Yes. Banana.”  
  
Dean thought of Jess. He breathed in and out.  
  
“Okay so – so what’s next?”  
  
“Oh, that’s it.”  
  
“I – what? That’s it?”  
  
“You got it!”  
  
“I grab anywhere – and then I banana.”  
  
“You’re totally sure you’ve never done this before?”  
  
Dean spluttered incredulously, “That can’t possibly be all the training! How do we even land?”  
  
Cas placed his hand on Dean’s side near the harness. “Eh, I’ll tell you all about landing when the parachute opens.”  
  
Shoving Dean out the door of the office, Cas looked at the group (Dean's eager audience) and his assistant. “Ready to go! You all know how to get to the drop site?”  
  
Sam stood up and confirmed ecstatically.  
  
Jess started taking pictures of Dean. He tried not to look like he was going to strangle his skydiver.  
  
“Damn, Dean, you’ve got your pump-up face on now!” Jo exclaimed, pulling out her phone for pictures of her own.  
  
_‘Yeah. Pumped up. Not wildly furious,’_ he thought, snorting.  
  
“You all can head out through the main door. Dean, you and I are meeting Ash out this way,” he said, motioning towards the back.  
  
“Ash?”  
  
“The pilot. Oh hey, Meg – “ Cas said, turning back, “Ash found the plane keys, right?”  
  
“Your pilot lost his keys???”  
  
Meg turned back to Cas casually. “Yup, about 20 minutes ago. He’s outside now.”  
  
Cas grabbed Dean by the wrist again – which was certainly not something getting any more charming – and led him through the final door, opening out to an enormous plane hangar and one single, tiny, misfit-toy plane.  
  
Cas rounded Dean to the other side of the plane where a large square hole led to the inside of the plane. Placing his palm on Dean’s chest – his hopefully not sweat-drenched chest – Cas gave Dean one quick look and down again, seemingly assessing his harnessing work before finally strapping himself up in his own harness with an enormous chute pack attached and covered in metal hooks down the front.  
  
Dean felt himself peer into the plane. There was no fucking door. There was no fucking door on this rinky dink plane, just a hole. A HOLE.  
  
“Dean,” Cas asked, voice muffled by a helmet he had slammed on while Dean was contemplating his life decisions. “Look at the camera!” he demanded, shoving a Go-Pro in Dean’s face with a red light blinking furiously at him.  
  
“Wait, do I get a helmet too?”  
  
Cas turned off the Go-Pro, “No, just me. Trust me, these things are just for show.”  
  
“But not show for me?” Dean was starting to have to yell over the sound of the airplane starting up behind him. Fuck, is there a pilot in there? When did a pilot get in there? Dean peered into the plane again where a ridiculous mullet-haired man-child sat in the driver’s seat.  
  
“What’s up, man! I’m Ash!” mullet yelled.  
  
“Dean,” Cas shouted to him over the blasting engines. “Just, look at the camera and say woohoo! Sound excited!”  
  
Fuck. This. Day.  
  
Dean looked back to Cas who was once again holding up the blinking Go-Pro. “You ready to do this Dean?” he shouted and smiled.  
  
Dean was totally going to vomit. He was going to fall out of a plane and vomit into his own face by gravity.  
  
Then again, that would definitely lead to his vomit flying up into the dickbag skydiver’s face.  
  
Win some, lose some, right?  
  
Dean felt himself let out a strangled and petrified, “woohoo,” which he was certain couldn’t have possibly sounded more fake or less enthusiastic.  
  
“Alright, let’s do this!” Cas shouted and climbed up into the plane, sitting himself on the raggedy, carpeted floor and spreading his legs wide. He patted the floor between his legs and looked up at Dean.  
  
“You’ve got to be joking,” Dean yelled.  
  
“Come on, baby, time to hop in!” Cas shouted back to him, offering out his hand. Dean reached out a shaky hand and squeezed his eyes shut tight. Fuck, he couldn’t do this. He had to, but he couldn’t. Every cell in his body felt like fire and ice as he felt Cas grab his hand and tug him up through the plane’s ridiculous excuse for a “door” (a hole. A fucking hole.)  
  
Dean felt Cas grab him around the waist and pull him close up against his chest.  
  
_‘Again with the manhandling,’_ Dean thought.  
  
The plane started moving. Everything came out of Dean’s control.  
  
Dean thought of Jess again. He breathed in. He breathed out.  
  
He didn’t notice himself digging his hands tightly into Cas’s thighs around his hips, didn’t notice himself drawing his knees up closer towards his chest.  
  
The plane left the ground. Dean felt his entire body shaking like a gong. He squeezed his eyes shut tight.  
  
Over the next while, Dean felt Cas shove him forwards and backwards, towards him and away from him checking and re-checking Dean’s straps and hooking Dean tightly towards his own harness.  
  
They must’ve been up there for half an hour when Cas shook his shoulder (okay, so maybe it was 4 to 6 minutes, but still).  
  
Dean opened his eyes – big mistake.  
  
Right outside the door-hole was about a mile high plummet to the ground. Dean heard a noise coming from his mouth – or was it coming from an animal? Or a tuba? He couldn’t be sure. It sounded like someone had run over a duck with a four-wheeler. Dean slammed his eyelids shut and his body back into Cas’ chest.  
  
Fuck this guy. Fuck this plane. Fuck Sam. Fuck himself. Fuck everything.  
  
And then came a surprise.  
  
Dean felt Cas wrap his hands around his shoulders and pull him softly back against him. Cas leaned forward.  
  
“Dean. You’re strapped to me. I’m going to take care of you.”  
  
Dean breathed in. He breathed out.  
  
It was a whole moment.  
  
Dean kept breathing and let Cas’s words wash over him. He was taken care of. Feeling warmth spread through his fingers, the tingling just slightly barely dissipate, Dean realized how intimate this entire experience was. Sharing his deepest fear with someone alone was tough for him, but sitting between their legs and shaking against their chest, their breath blowing against your neck –  
  
It was intimate.  
  
And weirdly hot.  
  
Which was pretty wonderfully distracting.  
  
Cas reached around and pulled Dean’s face towards his own – and Dean did the only thing he knew could possibly happen with that kind of face-reach move.  
  
Dean planted one on him.  
  
He used tongue.  
  
He used a little teeth.  
  
He pulled away, lips red, Cas’s eyes finally the ones shocked this time.  
  
Man, if this is how skydivers built up people’s confidence before a jump, Dean was certainly impressed – definitely surprised of course, but impressed with that kind of creativity. I mean, who wouldn’t be distracted and calmed and confident after getting kissed by a hot skydiver? Genius business tactic, really.  
  
But then.  
  
Cas bit his lip in a small grin and choked on a laugh, reaching around behind Dean to pull a pair a goggles from the back of Dean’s harness. He pulled Dean’s face further towards himself again and strapped the goggles around Dean’s head.  
  
Shit.  
  
FUCK.  
  
Dean couldn’t have been more mortified.  
  
Of course this guy wasn’t trying to fucking kiss him, Jesus Christ, _what was he thinking_? Cas settled on the strap tightness, still just barely containing his laughter, and gave Dean a light, friendly slap on the cheek.  
  
“Looks good to go,” he shouted, giggles escaping out.  
  
Dean scrunched his face up and felt blood rush up his neck to his cheeks. “Fuck.”  
  
Cas’ laughter filled the tiny plane and he reached up to tousle Dean’s hair. “Yeah, that was certainly a first for me.”  
  
Dean exhaled sharply through his nose.  
  
“Now – you ready for a first for you?” Cas bellowed. Dean’s eyebrows shot together before he felt Cas shove him forwards and around towards the door-hole.  
  
Oh god, it was happening.  
  
Every fiber within Dean froze up. What was he supposed to do again?  
  
It was some kind of fruit rule. Orange? Apple? Was he supposed to go fetal?  
  
Cas swung Dean’s legs to drape out of the plane.  
  
“Oh god, oh god, oh god,” Dean panted.  
  
“Banana!” Cas shouted.  
  
“What?!”  
  
“BANANA!”  
  
Dean wasn’t getting it. He stared out the door and wished the plane would just explode.  
  
“Oh for god’s sake,” he heard Cas behind him. Cas swung his feet around Dean’s shins, tugging straight and back, and clamped a palm over Dean’s forehead to bend him slightly into the plane.  
  
  
‘Oh yeah!’ Dean thought. ‘Banana!’  
  
And everything went silent.  
  
Cas launched them from the doorhole.  
  
The pair careened through the sky. Dean was pretty certain he was screaming, but the overwhelming silence – the quiet that came from the moment leaving the plane – deafened him and he had no idea what noise he was making.  
  
They fell. And fell. And fell.  
  
It was so goddamn fast.  
  
It was so much faster, so much bigger than he ever thought.  
  
Dean looked to his left and saw the blinking fucking Go-Pro around Cas’ wrist. _‘Goddamnit, Sam’_ he thought. He might’ve actually yelled it.  
  
And then he finally looked around –  
  
It was incredible.  
  
That moment of unbelievable silence, of vast earth and grass and sky, was broken sharply by a swift ballooning noise and a sharp tug on his harness (specifically at the groin – could’ve really used a warning there, dude). Dean’s legs swung forward into a seat and the breath was knocked out of his body.  
  
He definitely heard himself yell there – that was as close to a woohoo as anyone was going to get.  
  
Everything felt so much quieter.  
  
“Alrighty, Dean” he heard Cas say from behind, “How was that?”  
  
Dean swallowed and paused, catching his breath.  
  
“It – amazing. It was amazing.” He breathed in. “It was really amazing.”  
  
Cas chuckled. “I told you. Works almost every time.”  
  
Dean shut his eyes and let himself laugh.  
  
“Here, just take these for a second,” Cas said, lowering two yellow handles in front of him.  
  
“Um,” Dean mumbled, grasping the handles. “Okay?”  
  
Cas lowered his face down and forward to Dean’s ear. “Okay, Dean,” he said softly. “You’re driving the parachute.”  
  
Dean felt a burst of hysterics come from him.  
  
“I’m going to tell you where to pull and when, alright? When I say pull left, pull down on your left. You’re going to be fine.”  
  
“Pulldownleft? Forwardandleftorjustlikeforwardanddownandwhythough-“  
  
“PULL DOWN LEFT!” Cas shouted.  
  
Dean scrunched his face and let out a shout, yanking the left handle down and feeling himself and his chute swing down and left. Cas let out a loud woohoo ( _‘Maybe that’s what he was looking for for the video,’_ Dean thought) and Dean felt himself bellow in a laugh-shout.  
  
“RIGHT, PULL DOWN RIGHT!”  
  
Dean pulled down. He had never felt this way in his entire life – free and out of control at once, exhilarated and confident and calm. He’d never felt so cold and hot in the same moment. He and Cas and their chute swung through the air, looking over the Lawrence grasslands and the beautiful afternoon sky.  
  
And the ground.  
  
“Hey um, so, um,” Dean stumbled, “Landing? You said you’d tell me about landing now?”  
  
“Oh yeah!” Cas shouted, thrill and laughter in his voice. He was clearly having a great time, but goddamnit, he wasn’t telling Dean how to fucking land yet.  
  
“So uh – just stick your legs straight outward.”  
  
Dean did so. “Like this?”  
  
“Perfect! I might tell you to stand or run, so, you know, just do that if I tell you to.”  
  
“Are you fucking serious right now?”  
  
Cas laughed again. This guy laughed way too fucking much.  
  
Dean’s heart was beating out of his chest as they got closer to the ground – and suddenly he saw what seemed like everyone he knew at the drop site. The members of Sam’s car were there, sure – but also some of the other firehouse guys (the only ones not on the clock), the Roadhouse regulars, his friends from the neighborhood and from high school – all holding up signs, sparklers, confetti blasters, and screaming at the tops of their lungs for him. Dean threw his head back against Cas’ chest and laughed.  
  
  
And then they were on the ground.  
  
  
His shoes were filled with dirt, his eyes were blurry, but there they were on the ground, and before he knew it Cas had unclipped himself from Dean and stood up. Dean’s crowd sprinted up to him and all he could hear was yelling and questions and shouts of congratulations as he was ushered up into hugs.  
  
After a few minutes of, “Did you throw up, dude?” and “So you definitely pissed yourself, right?” and “I’m so so proud, Dean!” Dean had settled down and let himself calm down.  
  
He just couldn’t stop smiling.  
  
He looked over at Jess, currently piggy back on Sam’s enormous arms. He mimicked breathing in and breathing out. She smiled and winked.  
  
After he’d had enough celebration, after everyone had settled a little, Dean looked back at Cas and walked over. Cas was staring at the go pro and mumbling something to himself.  
  
“…fuck, how do I delete this, shit, I – oh, hey! You ready to head back to the station and pick up your stuff?” Cas asked, smiling and waving.  
  
Dean grinned, “Yeah. Yeah, man absolutely.”  
  
Dean would never have described himself as being bashful before. They both looked at each other, looked at their feet and left.  
  
“Well let’s go then,” Cas started and they headed over to the pickup van, Meg seated inside. Cas loaded up the enormous parachute, blown out like a homecoming dress. Dean waved goodbye to the crowd with a shout to meet at the Roadhouse in 30 and hopped in the van.  
  
Dean looked to his left and sighed – when an enormous bulldog crawled into his lap and drooled.  
  
“Um…dog,” Dean blurted.  
  
Cas chuckled. “Oh yeah, sorry. That’s Bonnie.”  
  
Meg started up the van, “We have to bring her with us on pickups – too needy otherwise.”  
  
Dean breathed out a small laugh. “She’s huge.”  
  
“Mmm,” Meg agreed. “There used to be a Clyde too.”  
  
“Meg,” Cas looked over at her.  
  
“What?” she snapped.  
  
Cas sighed. With Cas in shotgun and Dean directly behind him, Dean couldn’t see his face – so he pressed further.  
  
“Oh yeah? Another dog?”  
  
“Ha,” Cas laughed, clearly not humored. “Yeah, a dog. He stole my plane, left me here, and broke my heart.”  
  
“Classic Bonnie and Clyde,” Meg smiled.  
  
“Classic,” Cas smiled back at her.  
  
Dean’s eyebrows pulled together. Weird dog.  
  
  
The van pulled back into the airport lot and up to the Skydive front door. Meg led Dean back up to the office, and as Dean walked in he heard Cas stroll through the hall toward the hangar, open parachute in tow.  
  
They locked eyes. Cas’s mouth opened.  
  
“Alright, Dean Winchester,” Meg said, opening the door and moving behind her desk again. “Here is your phone, your keys, your wallet – anything else?”  
  
“Um –“ Dean looked around. Cas had left. “No, nothing else.”  
  
“Great,” Meg mumbled darkly. “Oh wait – hold on.” She ran into the back room and returned with the Go-Pro, taking a moment to quickly transfer the videos onto a USB drive.  
  
“Here you go, kiddo.”  
  
Dean made a face at the nickname and grabbed the flash drive. “Thanks. See you, uh…around.”  
  
“Mmmhmm,” she mumbled, staring back at the laptop.  
  
Dean took one last look at the door Cas had gone through – maybe he could just –  
  
“DEEEEAAN!”  
  
Sam was yelling from the Lawrence Skydive front door. “Come on, dude, Roadhouse!”  
  
Dean grinned and left, woohooing the whole way out.

  


Cas knew Dean had left.  
  
Dean had absolutely been the most beautiful tandem he’d ever had. And he’d fucking kissed him. God, that was just unfairly cute. Cas smiled just thinking about it.  
  
He knew he hadn’t given Dean his number – but he heard his whole gang talking enough about that bar down the road, the Roadhouse. He was sure he could accidentally meet him down there sometime. Cas snickered to himself.  
  
Laying onto the parachute to deflate the air, holding the cords at the sides to repack the chute, Cas chuckled at what he had almost done at the end of the drop – looking into the Go-Pro and leaving a ridiculous message. Fuck, come on – he was cooler than that. Thank god he deleted it.  
  
  
Wait.  
  
Cas dropped the chute.  
  
Fuck. Wait.  
  
Cas leapt off the chute, tripping forward on the fabric. “MEG!” he shouted from the floor, scrambling up and bursting through the door from the hangar to the main office. “MEG, MEG,”  
  
“Jesus, fuck, what??” she turned to him.  
  
“You – “ he panted. “You didn’t give him –“ he continued to pant.  
  
“Cas. What. Is. It.”  
  
Cas took a deep breath and slammed his weight through his palms onto the desk. “Did you give Dean Winchester his Go-Pro videos?”  
  
Meg paused and furrowed her brow. “Like I wasn’t supposed to?”  
  
Cas slammed his palms over his eyes.  
  
“FUCK.”

  


Dean stumbled back into his apartment at 8:30pm – it wasn’t exactly late, but hey, the party started at like 2 in the afternoon. And he’d put himself through basically a marathon worth of cardio (he was pretty sure that’s how that worked at least).  
  
Dean threw himself back onto his shitty couch. His apartment had felt so huge since Sam moved in with Jess – desolate and quiet.  
  
Fuck, he was too drunk for this much silence. And he was barely tipsy.  
  
Dean sighed and walked over to his bedroom, his tiny bedroom in his stupidly large apartment, and threw down the contents of his pockets to change into sweatpants.  
  
God, what an incredible day. What an amazing experience. And to have that experience end in drinking and sweatpants? Pure perfection.  
  
He looked over at the pile he’d tossed on his desk and saw the tiny USB drive.  
  
“Huh,” he mumbled. Chuckling to himself, Dean picked up the drive. “Might as well see the humiliation while I’m alone before Sam gets to it,” he said softly to himself.  
  
He watched the questioning of the helmet.  
  
He watched the pathetic woohoo.  
  
He watched the fall.  
  
All in all it was pretty funny – even Dean had to admit, in hindsight, he really loved it. I mean, it wasn’t _not_ due to the insanely gorgeous 6 foot tease strapped to his torso, but you know.  
  
It was amazing.  
  
He watched himself land, dirt clouding over the camera and smiled to himself, before seeing the camera cut off – and then immediately cut back on to Cas’ face staring over the camera.  
  
“Huh,” Dean let out.  
  
“Um,” Cas said into the Camera, panting, out of breath and laughing. “So, hi. You – um, you’re just absolutely gorgeous – you, you’re incredibly sexy and, um –“ Cas laughed to himself and looked up, shifting the camera and making some scuffling noise. “Okay, my number is 313-544-5923. I just, um – I – fuck, what am I doing,” Cas said, looking up and away and back.  
  
“What?” Dean said staring at the video gaping. He let out a bark of laughter and grinned wildly.  
  
Dean heard himself shouting and walking over in the video and watched Cas look back at the camera. “…fuck, how do I delete this, shit, I – oh, hey! You ready to head back to the station and pick up your stuff?”  
  
The video clicked off and ended.  
  
Dean went back and watched that section of the video 4 times before writing down the number.

  


At 8:30pm, Cas drove back to Lawrence Skydive to scramble through Dean’s paperwork to find his number and apologize.  
  
Which would make things even worse. And be kind of semi-illegal. Fuck. What was he thinking? Cas sat in the parking lot and let his head collapse onto the steering wheel before turning on his car to head back to his house empty handed.  
  
Maybe he’d go to the Roadhouse tomorrow.  
  
  
But then he got a text.

  


Dean had debated texting Cas for about 10 minutes before saying fuck it and texting him. _‘Why not?’_ he figured. _‘He made the first move.’_  
  
He smiled to himself. It was a big first move.  
  
**Dean** : Incredibly sexy, huh?  
  
He got a text back in under 30 seconds.  
  
**Cas** : This is Dean?  
  
**Dean** : This is Dean.  
  
**Cas** : Shit. I’m sorry.  
  
Dean hesitated.  
  
**Dean** : Uh…why?  
  
**Cas** : I meant what I said  
  
**Cas** : Not that I wouldn’t mean it – I just mean I had meant to delete it  
  
**Cas** : I had wanted to be cooler  
  
Dean snorted to himself.  
  
**Cas** : I’m cool. I just could’ve been cooler.  
  
**Cas** : Fuck, I’m making it worse.  
  
Dean smiled and felt blood rush up to his face.  
  
**Dean** : You’re fine. You’re “cool” I swear  
  
**Cas** : God damn it  
  
**Dean** : You’re too cool for school  
  
**Cas** : Okay, well, thanks for visiting Lawrence Skydive  
  
**Dean** : You’re the hostess with the mostest  
  
**Cas** : Hope you had a good skydive, bye  
  
Dean laughed openly. After a day of torment from this Cas, it felt really nice to be on the other side. Very satisfying.  
  
**Dean** : Oh come on, I can’t tease you a little?  
  
**Dean** : About how cool you are?  
  
Cas didn’t respond for 6 minutes. Dean started to text back a nervous apology before getting a reply.  
  
**Cas** : I’m sorry I gave you such a hard time  
  
**Cas** : I can be kind of a dick in these kinds of situations  
  
**Dean** : Situations…of doing your job?  
  
**Cas** : Situations of doing my job with someone so fucking hot  
  
Dean felt his face heat and bit his lip.  
  
**Cas** : fuck, I’m sry – shit  
  
**Cas** : Ive been pertty mad at myself fr not deletng that vid  
  
Dean laughed at the typos – Cas was clearly trying to type at hyperspeed.  
  
**Cas** : I was in the moment and it jst came out and I forgt to delet it  
  
**Dean** : Oh? You forgt to delet it?  
  
**Cas** : Dean.  
  
**Dean** : How flustered are you, like, scale of 1 to 10  
  
**Cas** : …  
  
**Dean** : Come on, Cas, fess up. Tell me how much you’re into me  
  
**Cas** : Wow, you’re the worst when you aren’t fearing for your life, aren’t you?  
  
Dean was smiling so hard he couldn’t contain himself.  
  
**Dean** : Cas, come on – these moves of yours  
  
**Cas** : Dean.  
  
**Dean** : Your moves work.  
  
**Dean** : Almost every time.  
  
Cas took a minute or so.  
  
**Cas** : Fine, I deserved that.  
  
**Dean** : Oh please, you deserve more than that  
  
**Cas** : Oh yeah?  
  
**Cas** : You goign to try to makeout wit me again?  
  
Dean’s eyes went wide.  
  
**Dean** : Hey, I thought you were making a move okay???  
  
**Dean** : It’s not my fault you ddn’t tell me goggles were going to happen  
  
**Dean** : You diddn’t tel me anything!  
  
**Dean** : You told me to wait fr landing information WHEN THE CHUTE OPENED  
  
Cas sent over a cry-laughing emoji.  
  
**Dean** : Don’t get all cocky over there  
  
**Dean** : You sent me a booty call video  
  
**Cas** : Oh my god, it was not a booty call video  
  
**Cas** : Just, hold on, I have to drive home from work  
  
Dean stopped himself.  
  
**Dean** : You’re still at work? Seriously?  
  
**Dean** : I thought I was your last skydiver of the day?  
  
Cas paused.  
  
**Cas** : I may have run back to work  
  
**Cas** : To try to find your number to ask for the video back  
  
Dean cackled.  
  
**Dean** : Any luck?  
  
**Cas** : Idk, you texted first soooo  
  
**Dean** : That means nothing  
  
**Cas** : Oh it means something  
  
**Cas** : You fell for my “booty call video”  
  
**Dean** : I thought it wasn’t a booty call vid  
  
**Cas** : It wasn’t. I was quoting you.  
  
**Cas** : Jackass.  
  
Dean bit his lip. Hard.  
  
**Dean** : Headed home?  
  
**Cas** : Yyyup.  
  
Dean looked at the clock. 9:17. It was early.  
  
He had beer and liquor. He had a couch and a TV and some confidence and his sexier jeans were clean.  
  
Well. Clean-ish.  
  
**Dean** : Would you want to not head home?  
  
**Cas** : Like…stay at work?  
  
Fucker.  
  
**Dean** : Like, come over here  
  
**Cas** : Here?  
  
**Dean** : My apartment  
  
**Cas** : You want me to come to your apartment  
  
**Dean** : I mean, if you want, whatever  
  
**Cas** : Whatever?  
  
**Dean** : Come on.  
  
**Cas** : What, are you going to ask to “Netflix and chill?”  
  
**Dean** : Ur a dick  
  
**Cas** : I mean, I love Netflix  
  
**Cas** : But as you said yourself, I am “so not chill”  
  
**Dean** : u  
  
**Dean** : Fuck  
  
**Dean** : Cas. Come over.  
  
Cas sent over a kiss blow emoji. And then a cry-laugh emoji.  
  
**Dean** : If you want I mean.  
  
**Cas** : Give me your address.

  


23 minutes later, Dean heard a knock on his door. Wearing his cleanish-sexy jeans, feeling confident that his apartment looked semi-not-like-shit, he swung the door open to find 6 feet of sexy, deliriously stressed skydiver in front of him.  
  
Laughing his ass off.  
  
“Wh-“ Dean started. “Why are you laughing?”  
  
Cas’s knees buckled. “I’m just – I’m remembering the face you made when I put your goggles on and –“ another gust of laughter burst forth and he fell against the doorframe. Dean felt bright red from his head to his toes as he sighed and smiled, closed his eyes and looked away.  
  
“God damn it,” he mumbled, licking his lips over his smile and trying to will away his furious blush. “Stop.”  
  
Cas laughed a second longer before running a hand over his face, smiling and chuckling as he looked over Dean.  
  
“If you were any sexier, I think…” he pursed his lips and grinned, “No, I definitely would still be laughing.”  
  
Dean let out a surprised bark of laughter before taking a single stride, grabbing Cas’s face at the sides and pulling him into a deep kiss.  
  
Cas stopped laughing.  
  
Dean pulled him into the apartment, tongues intertwining and Cas’s fingers running through Dean’s hair deliriously. Kicking the door closed behind him (which, holy shit, Dean could not believe he pulled that off) he slammed Cas into the nearest wall.  
  
Cas came up for air.  
  
“You’re jumping with me again, you know,” he told Dean, smiling like a maniac and tugging on Dean’s hair.  
  
“Out of… a plane?” Dean felt himself shouting.  
  
“No, jumping rope. Yes, out of a fucking plane,” Cas told him, diving back in for another kiss, desperately sucking to Dean’s lower lip before feeling Dean pull away.  
  
“Fuck. That. You – you are the worst! You are the least comforting person in the fucking worl-“  
  
“Oh, am I?”  
  
“Yes. You are.”  
  
“You jumped.”  
  
Dean stepped back, arm spread outward. “I was in the fucking plane strapped to you! I didn’t jump, I fell! I was pulled!”  
  
Cas grinned. “You. Jumped.”  
  
“I’m going to fucking jump you,” Dean spat under his breath.  
  
“Then do it.”  
  
Dean did it.  
  
Twice.

  


They hadn’t made it to the bed. That didn’t really surprise Dean. Cas was the kind of person who jumped out of airplanes for a living, so Dean wasn’t exactly shocked that Cas did things a little more excitingly.  
  
Sticky, sweaty, and feeling an odd combination of disgusting and satisfied, Cas and Dean had collapsed on his living room floor next to one another.  
  
“You’re such a dick,” Dean panted.  
  
“Wha? Why?”  
  
“You broke my coffee table.”  
  
“You threw me on your coffee table, jackass. You almost broke me, your table would’ve been a minor casualty.”  
  
“I didn’t throw you, you dropped! You fell!”  
  
“You and I seem to have a lot of disagreements about falling,” Cas said, tossing his head in Dean’s direction.  
  
Dean bit his lip and snorted.  
  
“You should just know – I liked your dog and all. I just – my apartment doesn’t allow dogs. And also she slobbered on me and all,” Dean told Cas quietly, sneaking his fingers through Cas’s.  
  
Cas furrowed his brow. “My d – oh, Bonnie.” He let out a huff of air. “Yeah, she’s…uh, yeah, she’s Meg’s.”  
  
“Oh!” Dean exclaimed. “I mean really, I do like her – she’s great, but she’s just –“  
  
“Oh I get it, you’re expecting me to move in because we slept together,” Cas teased. “You’re going to start planning the wedding tomorrow, right?”  
  
“What?! No!”  
  
“I mean obviously, you have to make sure my lifestyle wouldn’t violate your lease,” Cas said, crawling over to straddle Dean at the hips.  
  
“That is not. What I said.”  
  
“Me having a dog and all – too difficult for our potential children and – “  
  
Dean shoved hard and flipped them, leaving Cas breathless underneath Dean.  
  
Dean poked a finger to Cas’s chest. “I. Just. Wanted. To ask about your dog.”  
  
“Meg’s dog,” Cas returned.  
  
Dean rolled his eyes, “Meg’s dog. Yeah.”  
  
Cas sighed.  
  
“You have a thing with chest poking, Dean Winchester.”  
  
Dean laughed. “And you have a thing with being super annoying.”  
  
Cas laughed in return.  
  
Shit, he liked this guy.  
  
“I mean…she used to be my dog.”  
  
“What?”  
  
“Only sort of. Sort of my dog. Not actually my dog.”  
  
“How do you sort of have a dog?”  
  
“I don’t anymore.”  
  
Dean rolled his eyes. “How did you sort of have a dog, jerk.”  
  
Cas bit his lip.  
  
“I need to be drunker for this.”  
  
Dean looked at his clock. 11:35.  
  
“I think we could do that.”

  


2 fingers of bourbon later for Dean and 2 fingers of bourbon and 2 shots of horrible tequila for Cas:  
  
(Which, after shot number 1, went as following:  
  
_Cas: Oh my god, this is grotesque.  
  
Dean: Ha! I know, right?  
  
Cas: Why…why do you have this awful, horrible tequila?  
  
Dean: Um, duh, look at the bottle  
  
Cas: The sombrero?  
  
Dean: Yeah, man!  
  
Cas: This sombrero is plastic and like 4 inches wide  
  
Dean: Yeah. And it came with the tequila._ )  
  
Dean and Cas had settled on his couch, slipping closer and closer together since starting to drink. They’d fucked twice – and fucked well. Or at least Dean had thought so – why was he still so nervous? So skiddish? Sitting side by side in their boxers, thighs touching, arms pressed together, Dean still could barely contain his flush.  
  
It was totally just the booze, he told himself.  
  
“Okay,” Dean said, nudging Cas with his arm. “Tell me what you wanted to tell me but couldn’t.”  
  
Cas glared up at him through his unfinished glass of bourbon. “I could’ve told you, I chose not to.”  
  
“Uh huh. I could’ve been a skydiving instructor and chose not to. Go.”  
  
Cas rolled his eyes.  
  
“Agh…okay, so,” he started, shifting his feet onto the coffee table. “Bonnie was my dog. Clyde – Clyde was my…business partner.”  
  
Dean snorted. “You were fucking then?”  
  
Cas looked at his feet. “We were in love.”  
  
Dean paused.  
  
“Or I mean, no – I at least thought we were.” Cas paused and looked back up to Dean. “Don’t give me that fucking pity look.”  
  
“I’m not!” Dean defended, raising his hands with his glass shaking in one.  
  
Cas scrunched his nose. “He and I trained together at Skydive OK – it’s a skydive co. in Oklahoma.”  
  
“Yeah, I assumed,” Dean teased before getting a glare from Cas and miming zipping his lips.  
  
Cas smiled and rolled his eyes. “We were together, yeah – and we were actually planning on opening up Lawrence Skydive together. And then – I don’t know, something happened. I don’t know what happened, I just –“ Cas sighed and ran a hand through his hair. “He decided to take a risk. Go see his ex-girlfriend. In my plane.”  
  
“Ouch.”  
  
“Yeah, tell me about it. What’s worse is he took my plane. He stole my plane and fucking crashed it. Completely totaled.”  
  
“Oh my god,” Dean slipped. “Did he – he’s –“  
  
“Oh, he’s fine. He had a sprained ankle, broke his arm. But immediately cut off plans for the company with me. Cut off everything. He texted me for months though, trying to get me to move to fucking Boston with him to work in – in insurance or real estate or something less… I don’t know.”  
  
Dean looked at Cas sadly. “So he’s not…”  
  
Cas looked back up at Dean. “He’s not what?”  
  
Dean hated himself for this move. He gave Cas the puppy eyes.  
  
“He’s not… you’re not in love with him?”  
  
Cas gaped at Dean and turned. “Dean.”  
  
“What?”  
  
“Okay A. No. Absolutely not. He stole my airplane. He was an annoying shitbag. No, I’m not still in love with hm.”  
  
“I – yeah, okay, that’s great –“  
  
“And B. It’s been over a year for me to get this damn company started – this is still my first week in business, it’s taken me so goddamn long to get it-“  
  
“Hold. The fuck. Up.” Dean swung Cas around by the shoulders. “You’re telling me you’ve been running this company – this fucking company that I just jumped out of an airplane with – for a fucking week?”  
  
Cas snorted and immediately bit his lip.  
  
“I mean, I’ve been skydiving for over 9 years, Dean.”  
  
“A week? How did we even get reservations with you?”  
  
“We’ve had a website! We just haven’t been running!”  
  
“Oh my god, no wonder all your file cabinets were empty,” Dean mumbled, shocked and staring into the distance. Cas closed a hand over his mouth, smiling wildly.  
  
“I’m….sorry?”  
  
Dean glared at him. He tried not to smile. He tried really hard.  
  
“You’re not sorry.”  
  
“No, not for a second,” Cas said, laughter bubbling around his words.  
  
Dean shut his eyes and sank his head back.  
  
“I’m sorry about your plane,” he said to Cas.  
  
“I’m sorry I threw you out of my plane,” Cas grinned in response.  
  
Dean rolled his eyes again. “Oh please, you’re not sorry at all.”  
  
“Nope. Not for a second.”

  


Dean told Cas he would skydive once a year after that.  
  
He did it every year. But only with Cas, only with Ash flying, only in that shitty plane, and only with a super sexy hardcore makeout right before the goggles went on.


End file.
